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The opening of the epoxide ring of the 3,20-diketal of 16α, 17α-epoxy-Δ5-pregnene-3, 20-dione and of the acetate of the 20-ketal of 16α, 17α-epoxy-Δ5-pregnene-3β-ol-20-one with methyllithium has been studied. It was found that no products of the nucleophilic addition of methyllithium to the epoxide ring are formed, and after deketalization, 16-methyl-Δ4,16-pregnadiene-3,20-dione, Δ4,15-pregnadiene-17α-ol-3,20-dione, 16-methyl-Δ5,16-pregnadiene-3β-ol-20-one, and Δ5,15-pregnadiene-3β,17α-diol-20-one were isolated. The formation of the latter is due to alkali-catalyzed opening of the epoxide ring in the presence of the strong base, that methyllithium is.
KeywordsEpoxide Dione Methyl Iodide Organometallic Compound Nucleophilic Addition
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- 2.R. Sciaky, Gazz., 91, 562, 1961.Google Scholar
- 3.G. Amiard, V. Torelli, and J. Cereda, US 3, 104, 246; CA 60, 3060f, 1964.Google Scholar
- 5.A. A. Akhrem and T. V. Ilyushina, Izv. AN SSR, ser. khim., 192, 1966; 710, 1967.Google Scholar
- 6.L. I. Klimova, L. V. Sokolova, and N. N. Suvorov, KhPS [Chemistry of Natural Compounds], 289, 1968.Google Scholar
- 9.N. N. Suvorov, L. V. Sokolova, and N. V. Makarov, Izv. AN SSSR, ser. khim., 934, 1961.Google Scholar
- 10.K. Syhora, Collect., 29, 2351, 1964.Google Scholar
- 11.B. Hampel, Ber., 96, 2281, 1963.Google Scholar
- 21.Synthetic Methods in the Field of Organometallic Compounds, Vol. 1 [in Russian], 28, 1949.Google Scholar
- 22.K. Syhora, Collect., 26, 107, 1961.Google Scholar